Shy Guys Make Good Boys Pt. 02

I stared at her heels and for a moment, I finally broke a little. "No. No, please."

Her hand was strict again in my hair and I cried out in ecstasy when she slapped my face. "Ryan."

It was a whisper, every last awful word a trial. "Please let me sleep in my cage and toy to get used to it."

The only thing that made it bearable was that look of fire and hot pleasure in her eyes. "Good boy toy. That's such a good idea, too. Of course you can and I'll even reward you for asking." She used her soft touch in my hair to pull my mouth back to her pussy and I inhaled hot sex, blind with desire that wasn't getting release. It felt like hell.

It felt like fire hot heaven. She arched with the force of her orgasm when the exchange made her so horny and I clasped her closer, tongue fucking her frantically to help her draw every last second of bliss from her release in the ways she'd taught me to.

She was as bad as her word and I woke up in the night with another moment that made me realize that this comforted her, even while it made me whimper in torture. Because in her sleep, after dressing me in the toys, she was snuggled against my side where I lay on my back and she was petting the silky basketball shorts she had me wear to bed, over my cock cage. I lay still, trying not to shiver when it made me burn to think about, that she wasn't even awake and my torment was her calming drug. She was merely like a sleeping cat again, lightly pawing while she cuddled from her fill of playing.

Even more terrifying, I didn't have it in me to wake her. The thought alone was something I rebelled by submissive instinct. No, I carefully cradled her closer, shifting only slightly to give her easier access, holding back begging whimpers.

Another time, she took me to an ice skating show and later she called me over to teach me how to rim her asshole to orgasm, something that excited me, and by that time, I still hadn't had orgasm, so I was seeing red with lust and every lap of my tongue was a flick with a plea. I was desperate to please her because if she wanted me to suffer more at the end of this one, then the only satisfaction I could have would be her pleasure and I took of that with a sense of very real frenzy. She lifted off her bed, where she'd chosen to lay on her belly, fucking her hole back on my tongue with her release.

"Good boy toy," she cooed her pleasure. "That's not easy to do either." I stared up at her, dazed and shaking my head to clear it when all I could think of was how much I wanted to bury my nose against her pussy, when the scent was all I could think of. "Let's give you a reward."

That time she made me get on my hands and knees on the floor, fucking my ass with the plug while she jerked me off. "Cum for me. Show me how much of my good little anal slut you can be. You're already such a cum slut and cocksucking slut." I lifted a hand to clasp her arm closer to my chest where she held me, holding on for dear life with the force of that one.

"Thank you, Mistress. Thank you so much..." The words were degrading for the fact that I didn't decide to say them. They just happened in the midst of my ears ringing.

"Such a polite, good little plaything. Lick your cum off my floor." I crawled and did it.

That night I got to learn how to do her nails in a perfect manicure, while she quietly taught me what to do, letting me sit at her feet in contented happiness. She met my eyes with intimacy and tenderness after having sated her need for control. It was a cycle and it was one that I loved.

I admired her for it actually. You see, never once did she make it feel like my submission was a price I had to pay, even if it was something she seemed to need. No, see, she pet my hair too gently and took too much care in pressing my limits. She was too soft even when she was strict with her gestures. No, it wasn't like that at all.

It was more like she was thanking me for understanding somehow. The night when I did her nails I remember kissing her wrists and then her palms, glad that she'd let me take care of her somehow, when she was so proud. Like I said, I didn't fully understand, but I knew it wasn't always easy for her and I didn't want her to ever think I took it for granted.

She pressed her forehead to mine in reply and she didn't say the words that night, but I think it was the night we both kind of knew they were waiting in the background. It all just needed a push, one little nudge. We went through date after session after training after date after denial after teasing. I wouldn't say those words to push her comfort zone and she wouldn't say them when it would be stepping over into something deeper and she wasn't sure if that level was a good idea for us still. We fit together in a lot of ways, but that was one way where we certainly didn't.

Still, though, things find their ways.

By that, I mean, my idiocy forces them to happen.

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Sonya

It was the stupidest moment that finally shattered everything around me.

Courtney and I had a routine when it came to having that time of the month. We were both weirdly reactive to the same birth control, in the sense that we didn't have to deal with it as often, but we still sometimes had one and we somehow still ended up on it at the same time. So she'd come over and we'd be bitchy and judgmental together where no one else could see.

This time we were watching a trivia show and Courtney was wrapped around me. "Ugh. Sonya, I don't want to do things tomorrow. I don't want to people."

"You're a therapist. You have to people."

"Don't make me people, Sonya."

"I mean I guess you could just up and quit, but that'd be kind of shitty of you with a slake of appointments for a day."

She made a low growling sound and I laughed with how playfully whiny she got, lifting my phone when it lit up with Ryan's text. Feeling any better, Mistress?

I smiled with the thought that he knew how this went for me. I'd already dominated him during this time, choosing to wear jeans and boots the night before, and introducing him to the flogger across his cock, his balls, and his thighs. "Let's see if you can cum for me like this, baby." He'd been naked except for a blindfold and the good thing about being the one in control was that I didn't have to even explain why I wasn't fucking.

But, of course, Ryan knew me too well. When I'd had him on the floor of my toy room, I'd been soft, kissing up his thighs until he could get hard again. Something about this time of the month, when I didn't have it overly often, made me feel... just soft. I don't know another word for it. I'd felt gentle enough to suck him off when he got hard again, licking up his cock in slow, teasing laps, then opening wide to enjoy him. The rush of control it gave me to do it was different than the usual one, but it was still there with the thought of making him cum again, of seeing him lose control when I kept mine. It wasn't my usual thing, but during that time, it was something I felt like indulging in.

At the end, I'd petted him and his voice was soft where he sat at my knees, his face turned down. "Mistress?"

"Yes, little plaything?"

"Are you hurting?"

And it'd made me smile that he somehow had an idea of what was wrong, that I'd acted just a little too different or maybe flinched a little too obviously for the eyes of someone who bowed. "Not a lot, love."

"Would you like me to rub your shoulders and back?"

I'd let him do it, when those soft actions made him so content at the end of my training scenes, when he looked up to me during them with hopeful happiness, truly losing himself in the joy of getting those sweeter ways of serving me.

"Oh, so it's him." Courtney's voice pulled me from my thoughts and I grinned sheepishly, so that she laughed, picking up a Hershey's Kiss.

"He's being adorable again."

"Ugh, I saw him in Sulfur's. That baby face is freaking killer in person, it really is."

"I told you."

I am, love, thank you. Not so bad today. And how are you doing?

When I looked up from answering, Courtney was watching me, a small, evil smile on her face. "What?"

She shrugged. "Not a thing, doll."

My phone lit up with his answer. That depends.

On what, little boy toy?

I looked up with the knock on the door and Courtney lifted up from the couch, her long hair braided back like mine was when we'd both decided we liked that hair style. She was laughing. "Wow, I wonder who that could be? This is fun. I bet he doesn't know he's walking into the lion's den."

I threw a Hershey's Kiss at her. "You play nice. He's being sweet."

She snickered. "Oh, but that's when they don't want you to play nice."

It made me grin when I opened the door and he was standing there. "It depends on if cupcakes would cheer you up, Mistress," he said softly, his eyes playful while he held up the box.

Courtney answered before I could, going to the door behind me. "Are they chocolate?"

Ryan froze and it was truly an adorable moment for the small fact that it was so... I don't know, basic. I had to grin when he swallowed, when he bit his lip before he answered. "I should have brought more cupcakes."

Courtney burst into happy laughter and grabbed him by his collar so that I stood to the side, watching him look back at me with his eyes begging me. "God, you really are the cutest damn thing. And so sweet, too. You did her nails last night." Ryan nodded, wide eyed, and I realized he wasn't sure how to address her. "It's so pretty. I want one of you, little plaything."

"I don't like pain, please," he answered instantly and it made me laugh in happiness, while Courtney looked to me in outrage, shoving him down so that he was forced to kneel at her feet.

"Why do they always think I'm going to hurt them? They always think that."

"Because you always hurt them."

Ryan's voice was timid. "May I ask something?" Courtney tilted her head. "Your playmate." He seemed to rush through it, to make himself ask the question. "Does he ever get to finish or do you really only let him have the cane?"

Her smile was wicked and she tightened a hand in his hair. "Wicked, too. I really like you, little boy toy."

I felt flirty and it was a moment of fun, even if none of us had the intention of going anywhere with it. Ryan shuddered when I stroked him from behind, shoving a finger between his lips. "I think he likes the thought." His eyes widened and he looked up at me desperately, shaking his head while he sucked gently at my finger. "No? Are you sure? I could always unlock your cock cage and find out for myself." He moaned at that and Courtney giggled, petting his jaw.

"To answer you, love, he really doesn't get to orgasm. He only gets to enjoy the amount of pain he can take for me while I get off on giving it. It's intoxicating, the way the sadism high is so intense." She grinned at him. "I don't even really like getting off any other way anymore, if I'm being honest. Sometimes, I don't really want it to end when it just feels better than sex to give pain."

Ryan stared at her and I knelt down behind him to kiss his neck. "Forgive her. Sadists are weird."

She grinned. "I'm not nearly as mean as Sonya is sometimes, though. Sure, I'm evil about pain, but Sonya can be way more degrading. Different approaches and all that." She pet his hair to comfort him, evidently in her own mood of softness. "He was a strange one when he found me. It started out with curiosity from Venus in Furs after he found the book and he wanted to know what the real thing felt like." She smiled. "He liked what it felt like and it went from there. I can play banter and tease, but I don't do things without talking them through first."

Ryan tilted his head with that same curiosity he'd had when I'd found him talking to Christopher at Sulfur's, so that I had to smile. He had these little habits, these tics when his thoughts took off from him. "I'm glad he likes it then," he said softly. "And with a way that's safe. It seems like there's too many stories online that people claim are real that make you hope to God they're not." He made a face. "I have to be honest. I stop reading true accounts - when I'm trying to write believably - if they use the phrase 'the natural order of humanity'. Indoctrination just doesn't seem all that safe to me."

Courtney burst into laughter. "Oh, I like you. I like you a lot."

He grinned in that puppy like way, pleased with himself in a way that made me laugh in his ear and kiss his neck so that he tilted his head and exhaled, another tell-tale sign of his. Although this one was one that went with the effect of his cock cage tightening around him when I aroused him. "I can't say I like the gateway drug book of choice he had though."

"No? Wanda not the Mistress to your liking?" Courtney grinned.

He made a face. "What the fuck was that ending? It makes me angry. Who goes to porn for a shitty ending? No one, that's who. No one goes to porn thinking, 'I hope the husband ruins the wife's life after she finally tries assfucking'. At least not in visual porn. But can books give the courtesy of following the rule? No. Apparently not. They have to be all hipster about it. Wanda was downright cruel, not anything like Mistress, and she wasn't so full of love at all-"

He snapped his mouth closed, going still, and Courtney's grin couldn't have looked more wolf-like. "Wow, you both seriously hadn't said it yet, had you? Jesus, you're idiots. I just had to see Sonya look at her phone over the past month to get it."

Ryan turned his head to look back at me and she let him, releasing him. His eyes were wide and worried, but I couldn't keep from smiling. "Love is probably a very good word," I said quietly.

I'd been afraid of crossing a certain line, afraid of where it might lead. Because if I crossed that line, I went into the territory of something that would be painful hell to leave, and not in the good way. If I crossed that line, it felt like something deeper than what we'd been having, a lot deeper.

Except, when he said the word, even if it wasn't that three word phrase, my heart leapt in happiness. He got me. Somehow, I'd found someone who understood. Somehow, I'd met someone who could put up with my control freak shit, as much as I used it to comfort myself and keep tight hold on my own control. "Do you want me to train you, Ryan, actually train you?"

His eyes lit up with excitement. "Yes, please." And his voice was so eager, even while he kept it soft. "Yes, I would like that."

"Alright. Hang out with us tonight and then I'll tell you tomorrow how it will go."

His excitement intensified when I didn't offer him a say in it and he nodded happily while Courtney leaned forward again to stroke his hair. "You might regret that. I'm telling you that Doms can be more sadistic than a sadist by proxy, love."

He leaned back against me and his voice was soft, so soft, in that way that came with the moment right before he fell into subspace, when he was always so easily pushed into it now. "I'm okay with that."

I stroked him, thinking that I needed to break the moment, thinking that tonight wasn't a scene. Although, maybe, on second thought, I could make a kind of game out of it. "Courtney, lay down on your stomach." She glanced at me, shrugged, then did it, laying still. Ryan shivered when I grabbed his hands and pressed them to her lower back, lifting her shirt up.

Obediently, he rubbed her down in that soothing way I'd taught him to do with me, so that he got to indulge in one of those softer forms of serving that he loved so much. Courtney purred happily, so that he smiled.

"Oh, God, and he does massages? Sonya, I want one."

"Get your own. This one is mine now."

He practically radiated his pleasure with the thought, too. Well. We'd been dating in that gray area for months by then. Maybe it was really just about time anyway. I caved, I gave in, and the armor shattered. Although, I couldn't say I felt all that awful without it.

Maybe it had always been a little too suffocating to keep myself in that stranglehold anyway.

--------

Ryan

Her text hadn't given much away, in the sense that it didn't let me know entirely what she had in mind for me. All I had to go off of was the tone in what she had said. You're staying with me weekends, Tuesday nights, and Thursday nights until I'm done. You can safeword your way out at anytime. That's something that doesn't change, love.

Yes, Mistress.

When I went to her place for that first weekend that she set it, it was enough time that her time of the month had ended. Courtney wasn't there anymore and somehow, that felt like a frightening thought, that it was just her and I and no one to stop her once she got started, when I was hers once she did get started. I went to her with a sense of being locked in a far more permanent harness, a collar around my throat that wasn't coming off anymore.

Although, maybe it was silly to feel that way, when I'd been wearing her collar this entire time, since the start, when it fit just fine under my leather jackets and I could get away with it at work even, when I wanted to, along with her cock cage. She hadn't told me to, no, but it had always been there.

"Good evening, Mistress."

She smiled and I would say that I'd gotten used to how she could look in those short dresses and boots, but I didn't think I ever would. No, I thought she would always look like my personal temptress in that outfit, but maybe that had a good deal to do with my orgasm denial and how it was a double edged sword when being denied made me hot.

"Good evening, love. You sure you want to do this? We can go on a date instead." Her smile was soft and sinful all in one. "Check your courage."

I swallowed with the repetition of the wording when the last time had come with my introduction to anal sex. Of course, now I had a fair bit of experience with wearing a toy in my ass, with that sensation of fullness, and she had gotten larger and larger with the toys she used to train my asshole. "I'm sure I want to," I whispered back.

It was hot, so hot, looking down at her when she was right from before, when she had already mentioned how much she enjoyed my being larger than her when it meant I could get away from her, when there had never been anything stopping me from taking the key around my neck and freeing myself, stopping all of it. Except Iwouldn't. And that was the hot part about it.

"Brave boy toy," she purred back, reaching up to stroke her hands up through my hair so that I lowered my head obediently with her gentle pull, wondering again at the pieces of the puzzle that made up my role in this, of that strange background image that was comprised of a few different pieces. It had to do with sitting at Christopher's knees and enjoying my hair being pet in a manner that had nothing to do with sex and everything to do with guiding control, those moments where I realized that she was giving me safewords to be so careful and I was being bad somehow when I wasn't safe at all because I couldn't stop her. It had something to do with how I craved to be led and to serve while she needed to control to let me do that. It was two puzzle pieces that fit together, jagged edges and strange flaws that shaped around each other, blending together in a way that felt like magic. And it did feel like magic. To look at us separate, one would think we were immiscible, and yet...

I held her close in the way she had taught me she liked the most, stroking a hand down her braid with a smile at the memory of all my Mord-Sith fantasies and placing the other at the small of her back, protective in one way without any of the taste of dominance that seemed to be mistaken for protection. It had started to feel like a dance with her if I'm honest, the balance beam of control and soft moments when she was delightfully proud and wonderfully wary.